Potassium Carbonate → 5-fluoro-2-[1-(2-chloroethyl)-5,6-dimethoxy-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 490458Notes

Reaction equation

HRID 490458 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[NH:8][CH:7]=[C:6]2[C:14]1[N:23]([S:24]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[C:17]2=[N:18][CH:19]=[C:20]([F:22])[CH:21]=[C:16]2[CH:15]=1.[OH-].[K+].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:43][Cl:44].[CH3:45]O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCCl>[F:22][C:20]1[CH:21]=[C:16]2[CH:15]=[C:14]([C:6]3[C:5]4[C:9](=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:8]([CH2:45][CH2:43][Cl:44])[CH:7]=3)[N:23]([S:24]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)(=[O:26])=[O:25])[C:17]2=[N:18][CH:19]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 21226129Dichloromethane methanolHCID 671475792-(5,6-dimethoxy-1H-indol-3-yl)-5-fluoro-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 671475755-fluoro-2-[1-(2-chloroethyl)-5,6-dimethoxy-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

But using 2 g of 2-(5,6-dimethoxy-1H-indol-3-yl)-5-fluoro-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine, 0.028 g of tetrabutylammonium bromide, 1.89 g of potassium hydroxide and 1.38 g of potassium carbonate in 50 ml of 1,2-dichloroethane. After flash chromatography on a silica column [eluent: dichloromethane/methanol (98.5/1.5 by volume)], 2.05 g of 5-fluoro-2-[1-(2-chloroethyl)-5,6-dimethoxy-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine are thus obtained in the form of a solid, the characteristics of which are as follows:

Sources & evidence

ORD record
ord-0164c11599b443b7a19b8b46d090e4ad
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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